HOME
login
history
all enzymes
BRENDA home
History
Information on EC 5.1.99.3 - alantoin racemase
for references in articles please use BRENDA:EC5.1.99.3Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
5.1.99.3 alantoin racemaseSpecify your search results
Word Map
- 5.1.99.3
-
racemization
- allantoinase
- purine
- urate
- allantoate
-
enantiomer
- utilis
-
nonenzymatic
- deae-cellulose
- sephadex
- isomer
-
klebsiella
-
uric
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
allantoin racemase, AllR, BFW91_04965, HpxA, HpxA enzyme, KPN_01788, Racemase, allantoin, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AllR
BFW91_04965
HpxA
KPN_01788
Racemase, allantoin
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)(+)-Allantoin = (R)(-)-allantoin
-
-
-
-
(S)(+)-Allantoin = (R)(-)-allantoin
mechanism of enzymic racemization differs from that of non-enzymic racemization
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
racemization
racemization
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
Allantoin racemase
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
56214-40-5
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(R)-allantoin
(S)-allantoin
-
-
-
-
r
(S)-allantoin
(R)-allantoin
-
-
-
-
r
additional information
?
-
-
stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
-
-
-
additional information
?
-
-
stepwise reaction mechanism via a planar unprotonated intermediate. A pair of cysteine residues promotes the stereoinversion of a carbon atom of the ligand without the assistance of cofactors, quantum mechanics/molecular mechanics calculations
-
-
-
additional information
?
-
Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
-
-
-
additional information
?
-
Allantoin can undergo racemization through formation of a bicyclic intermediate (faster) or proton exchange at the chiral center (slower). The velocity of the reaction via a bicyclic intermediate is unaffected by the enzyme, whereas the velocity of the reaction via the chiral center is increased by 7 orders of magnitude
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.4
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
1.1
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
2.3
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
0.3
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
2.5
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
43
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
57
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
238
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
129
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
183
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
19
(R)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(R)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
595
(R)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
16
(S)-allantoin
mutant E78D, pH 7.6, temperature not specified in the publication
52
(S)-allantoin
wild-type, pH 7.6, temperature not specified in the publication
610
(S)-allantoin
-
in 10 mM NaCl and 10 mM HEPES, pH 7.5, at 25°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20 - 60
-
20°C: about 35% of maximal activity, 30°C: 67% of maximal activity, 60°C: about 85% of maximal activity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene hpxA is not essential for growth on allantoin
UniProt
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
conversion of allantoin to allantoate is the second of the two ring-opening steps in purine utilization
physiological function
mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
physiological function
-
mechanism of racemization involves residue Glu78 acting as a base for the abstraction of the C5 proton of (S)-allantoin and Cys 180 transferring a proton on the opposite side of the allantoin ring. In the stereoinversion of (R)-allantoin, proton abstraction is performed by Cys 180 and reprotonation by Glu 78
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
Sequence
A0A2H1JPH0_9MICO
241
0
25331
TrEMBL
E1V7D0_HALED
Halomonas elongata (strain ATCC 33173 / DSM 2581 / NBRC 15536 / NCIMB 2198 / 1H9)
246
0
25925
TrEMBL
A0A4S7X8W8_KLEPN
247
0
25804
TrEMBL
A0A0P0RBK5_9BURK
285
0
30220
TrEMBL
A0A2H1IMG0_9MICO
275
0
27999
TrEMBL
A0A1Y0PXM4_KLEPN
247
0
25790
TrEMBL
A0A0S2W885_9FIRM
217
0
23208
TrEMBL
A0A427BZJ8_9ENTR
244
0
25344
TrEMBL
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexamer
hexamer
-
trimer of dimers, X-ray crystallography
-
hexamer
-
trimer of dimers, X-ray crystallography
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CRYSTALLIZATION/commentary
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 24-34% (w/v) polyethylene glycol 400 with 0.1 M sodium acetate, pH 3.7-4.1
-
in cubic and orthorhombic crystal forms, at 2.10 and 2.15 A resolution, respectively
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C79S/C184S
-
the double mutation leads to total loss of activity
C184S
-
the mutation leads to total loss of activity
-
C79S
-
the mutation leads to total loss of activity
-
C79S/C184S
-
the double mutation leads to total loss of activity
-
C184S
-
the mutation leads to total loss of activity
-
C79S
-
the mutation leads to total loss of activity
-
C79S/C184S
-
the double mutation leads to total loss of activity
-
E78D
mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
E78D
-
mutant shows diminished catalytic activity affecting kcat and KM for both enantiomers
-
additional information
additional information
gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
-
gene insertion mutant, gene hpxA is not essential for growth on allantoin
additional information
-
gene insertion mutant, gene hpxA is not essential for growth on allantoin
-
additional information
The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
additional information
-
The Pseudomonas protein lacks a cysteine residue (C79 in the Klebsiella pneumoniae AllR sequence) that is essential for the two-base catalytic mechanism of KpAllR. The residue is substituted with glycine
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION/commentary
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED/commentary
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme belong to a 23-gene cluster that encodes the enzymes for utilizing purines as the sole nitrogen source
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Okumura, I.; Yamamoto, T.
Enzymic racemization of allantoin
J. Biochem.
84
891-895
1978
Cyberlindnera jadinii
brenda
Van der Drift, L.; Vogels, G.D.; van der Drift, C.
Allantoin racemase: a new enzyme from Pseudomonas species
Biochim. Biophys. Acta
391
240-248
1975
Comamonas testosteroni, Pseudomonas fluorescens, Pseudomonas putida
brenda
Pope, S.D.; Chen, L.L.; Stewart, V.
Purine utilization by Klebsiella oxytoca M5al: genes for ring-oxidizing and -opening enzymes
J. Bacteriol.
191
1006-1017
2008
Klebsiella michiganensis M5al (B5B0K3), Klebsiella michiganensis M5al, Klebsiella oxytoca (B5B0K3), Klebsiella oxytoca, Klebsiella oxytoca M5al (B5B0K3)
brenda
French, J.B.; Neau, D.B.; Ealick, S.E.
Characterization of the structure and function of Klebsiella pneumoniae allantoin racemase
J. Mol. Biol.
410
447-460
2011
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae MGH78578, Klebsiella pneumoniae subsp. pneumoniae Trevisan MGH78578
brenda
Cendron, L.; Ramazzina, I.; Puggioni, V.; Maccacaro, E.; Liuzzi, A.; Secchi, A.; Zanotti, G.; Percudani, R.
The structure and function of a microbial allantoin racemase reveal the origin and conservation of a catalytic mechanism
Biochemistry
55
6421-6432
2016
Pseudomonas fluorescens (E3SAZ9), Pseudomonas fluorescens DSM 50090 (E3SAZ9)
brenda
Bovigny, C.; Degiacomi, M.T.; Lemmin, T.; Dal Peraro, M.; Stenta, M.
Reaction mechanism and catalytic fingerprint of allantoin racemase
J. Phys. Chem. B
118
7457-7466
2014
Klebsiella pneumoniae subsp. pneumoniae, Klebsiella pneumoniae subsp. pneumoniae ATCC 700721
brenda
Select items on the left to see more content.
EXTERNAL LINKS (specific for EC-Number 5.1.99.3)
html completed
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Information
